Vat dyestuffs and process of making same.



UNITED STATES PATENT OFFICE.

BENNO HOMOLKA, Q3 FBANKFORT-ON-THE-MAIN, GERMANY, ASSIGNOR TO FAIRB- WERKE VORM. MEIBTER LUGIUS 1!, BBU'NING, OF HUGI-IST-ON-THE-MAIN, GERMANY,

A CORPORATION OF GERMANY.

VAT DYEBTUFFS AND PROCESS OF MAKING SAME.

1,209,;63. R0 Drawing.

To all whom it may concern Be it known that I, Bruno HOMOLKA, Th. D., chemist, a citizen of the Em ire of German residing at Frankfort-on-the- Main, ermany, have invented certain new and useful Improvements in new Vat Dyestuffs and Processes of Making Same, of

which the following is a specification.

v The new body thus obtained may, therefore, be regarded as dimethyl-dianilinoquinone and constitutes the most simple representative of the dime'thylrdiarylamind quinones obtainable by the process above referred to.

The above-mentioned reaction occurs on heating in an aqueous solution; however as both the para-quinones and the arylaminoacetic acids are scarcel soluble in water, it is advisable to use sucli organic solvents as can be mixed with water, such, for instance, asmethyl-alcohol, ethyl-alcohol, acetic acid or the like.

The followingexamples illustrate my invention, the parts being by weight:

Ewample I-Vat dycstufi' from ben'zoquinone and phenyla-mz'no. acetic acid (phenylgl cin).-100 parts of benzoquinone are dissolved in a mixture of 500 parts of alcohol and 100 parts of water, whereupon parts of phenylamino-acetic acid (phenlyglycin) are added and the whole heated. When the heat has risen to about 40-5Q C., a violent evolution of carbonic acid sets .in, upon the termination of which the whole is further heated to boiling for about onehour. After cooling, the dycstutf which has separated is filtered ofl', washed with alcohol and dried. The dyostull' thus btained forms brown crystals melting at 232 C. with decomposi- Specification of Letters Patent.

, resulting dyestufl' is filtered off, washe Patented Dec. 19, 1916.

Application filed July so, 1915. Serial No. 42,754.

tion: It is insoluble in water, in dilute acids and alkalis, almost insoluble in the usual organic solvents of a low boiling point, such as alcohol ether, acetone, benzene, however readil soluble with an orange-yellow color in boi ing glacial acetic acid and xylene, and with a red color in concentrated sulfuric acid. The dyestufl' gives, when dissolved in an alkaline solution of hydrosulfite, a colorless vat which dyes the animal hber fast yellow tints.

Ewamplc Il.-When using 100 parts of benzoquinone and 55 parts of ortho-tolylamino-acetic acid (ortho-tolylglyein) and working in the manner indicated in Ex-' ample a reddish'brown crystalline body is obtained which melts at 243 C. with decomposition and possesses the same pro erties as that obtainable according to xample 'I), being, however, distin uished from the latter by the bluish-re color of its solution in sulfuric acid. The new body may be regarded as dimethyl-di-orthotolyl-diaminoquinone (dimethyl di ortho- V toluidino-quinone) it dyes in the vat wool yellow tints.

Example [IL-Dyestu/f from dicklorogal-none and pkenylaminomcetic acid (pheng 7gZ-ycin).-75 parts of dichloro-quinone and .135 parts of phenylamino-aeetic acid (phenylglycin) are dissolved together in acetic acid of per cent. strength and heated in the water bath. After coolin the with acetic acid and with waterand dried. The new body, which is to be regarded as dimethyl-dianilino-dichloroquinone, is fusible with extensive decomposition,,without any precise melting oint; it is insoluble inwater, in diluted acids and alkalis, almost insoluble in the usual organic solvents such as alcohol, ether, acetone, benzene, soluble 1n concentrated sulfuric acid with .a violet color. It dyes in the vat Wool yellow tints. A quite similar dycstutf is obtained by using instead of'75' parts of dichloro-quino'ne, 100 parts of chloranil.

Having now described my invention, what I claim is: a

1. The process of making new vat dye stuffs, which consists in heating paraquinoneswith arylamino-acctic acids in a suitable solvent.

2. As new commercial products, dimethyldiaryl-amino-pamuinones, which constitutc brown crystal inc powders, bcin in soluble in water, diluted acids and 01 11115, nwtimllyimulublc in alcuhol, cthcr and 611mm, soluble with u bluish-red color in ccncntI-i tcd culfuric acid, and yielding cciurlcss vats which givc yellow tints on ihc animal fiber.

8. As a new commercial product, the vat dycstufl of the formula:

which consuming a brawn ci'yslalling; qw-

(lcr u cl tiqg at} 232 with dgcompcs 10p,

momma being insoluble in water, in diluted acids and alka is, practically insolublc in alcohol, exhar and bnngomw oluble with an w ngeyallcw wlvr n bmlmg ylfil mi E 5 cpic ccppcntxated sulfuric aci yieldm W cm dissolved in an alkaline wluticn o hydrosulfite, a colorless vat which gives yellow: tints on the animal fibm'.

In tgs timon whereof I affix my signi pui c 25 in presence 0 two witnesses.

BENNO HOMOLKA. Witnesses:

gun GRUND m Grimm). 

